Working on the Road: 4 Tips for Freelance Writing While Traveling

As I write this, I’m at Chicago’s O’Hare International Airport waiting for the next leg of my journey out to the East Coast. As a location-independent freelancer, I always try to take full advantage of travel interludes to catch up on my work.

Working on the road can be a tricky endeavor. It’s amazing to be able to work from anywhere with a WiFi connection, but it’s important to plan ahead to be able to enjoy work and play while traveling. Trekking through Machu Picchu is a whole lot less exciting when deadlines are weighing you down.

No matter how location-independent you are, working from the road definitely has its share of challenges.

Here are a few tips I’ve learned along the way to help balance work and travel.

1. Plan before you go

Before I leave home for a trip, I always pull a few lists together. I use old fashioned pen-and-paper, though many prefer digital to-do lists and programs such as Evernote (which still live in the cloud if you spill coffee all over your notebook).

The first list I pull together is a list of deadlines that need to be completed while I’m away, urgent emails and phone calls I’ll have to find time to return, and other important items I can’t forget.

I always try and get as many of these sorts of things taken care of as possible before I leave, but things have a way of coming up at the last minute.

Whether it’s an urgent revision request for an article turned in months ago, or an email from the person you’ve been trying to track down for a month saying they have a small window of availability for an interview before they move to rural Botswana, sometimes things pop up on the road that you have to take care of.

The second list I pull together is a list of offline tasks I can do. Generally, this involves “deep work” such as writing and non-web research, which is best done without online distractions such as pinging messages and emails — or the ever-present temptation of surfing the web. These tasks are great for airplanes. I don’t opt for expensive airline WiFi, though many freelancers swear by it.

I find brainstorming also works very well while traveling. An infusion of newness and a disruption in one’s daily routine can allow for a lot of creativity. The change in scenery lends well to brainstorming, whether it’s mapping out an article, thinking of new articles to pitch, or adding a new twist to the novel you’re writing.

2. Stick to a schedule

When you are lucky enough to be able to work and play, you sure don’t want to blow it. That’s why it’s important to schedule your time and plan so you can make the most of both work and play.

When I’m traveling, I like to do a little work first thing in the morning, and then check for any urgent emails I need to respond to in the late afternoon. Many times, I’ll be in locations with limited internet access, so I’ll check my emails whenever internet is available. It’s also important to take some time offline in order to disconnect and recharge.

If I need to put a solid chunk of work in on a project, I’d rather do that first thing in the morning so I have the rest of the day free to wander around and play without worrying about making a deadline. It also gives you the freedom to go explore the local nightlife without stressing about your assignment.

But that’s just my personal preference. Some night owl writers prefer the opposite schedule. Experiment and find what works best for you.

But be sure to stick to your scheduled times for work and play. You don’t want to fall down the rabbit hole of email and spend your trip responding to emails instead of seeing the sites of Belarus, Bangladesh or the Bahamas.

3. Communicate with clients

So, you’re leaving town. What do you tell your clients? Well, that depends on your work plan. Will you be scheduling a few hours for work every day and be available for routine, day-to-day inquiries? In that case, you may not need an away message at all.

But if you’re going off the grid, be sure to set an away message on your email and voicemail so clients know why they’re not hearing back from you right away. Be sure to let them know when to expect a response. If you have a back-up for urgent matters, be sure to list that person’s information.

If you’re planning on going off the grid for a significant amount of time, you should communicate this to clients well ahead of time so they can work with you to wrap up any loose ends before you head out.

4. Back it up

When you’re working from the road, it’s important to have dependable access to your files. I always have a few options available and I plan for different contingencies.

Before I head out, I load important files that I’ll need onto my mini travel laptop. Then, I copy these files to a flash drive I also take with me. I figure if the laptop conks out, I can take the flash drive to a hotel business center or internet cafe with the files to get my work done if need be.

As another layer of protection, I also have the files uploaded to my Dropbox account, so I can access them digitally if I need to. While none of these solutions is foolproof, having some redundancy in my data storage makes me feel much better when I work on the road.

Do you spend a lot of time working while traveling? What tips and methods do you rely on?

Kristen Pope is a Jackson Hole, Wyoming based writer and editor. Her work has appeared in Discover, Backpacker, Western Confluence, International Journal of Wilderness, and Planning Magazine, and she is the managing editor of JHStyle Magazine.

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12 comments

Hi Kristen,
Love the post, a great practical reminder of the realities of the frequently glamorised location independent lifestyle. I particularly like the idea of batching tasks that can be done offline. Maybe I’d be best spending more time offline, even when not travelling! Thanks for the practical advice.

These are great tips. I am leaving in one week for Salt Lake City to accompany my husband on a business trip. I get time to explore each day while he is at a conference so I am definitely going to use your tips as I prepare for the trip. Thank you!

“Stop thinking about it and do it!” As a writer, my favorite option is, of course, freelance writing 🙂 I would also suggest looking beyond places like Odesk and Elance, and using sites and Google to research prospective customers, so that you could earn even more – though it could take longer, of course. I like that you explained here that it takes a long time, that making a full time living when you set off on your own doesn’t happen overnight. People who want to travel long-term and rely on income from many of the suggestions here will probably be better off taking time to prepare in advance. Great list!
“Trust that things will work out. They always do one way or another.”

It was the kind of pure, undiffused light that can only come from a really hot blue sky, the kind that makes even a concrete highway painful to behold and turns every distant reflective surface into a little glint of flame. Do you know how sometimes on very fine days the sun will shine with a particular intensity that makes the most mundane objects in the landscape glow with an unusual radiance, so that buildings and structures you normally pass without a glance suddenly become arresting, even beautiful? Well, they seem to have that light in Australia nearly all the time.